The invention relates to novel biphenyloxazolines, to processes for their preparation and to the use of the biphenyloxazolines for controlling animal pests.
It is known that certain biphenyloxazolines have insecticidal and acaricidal activity, for example the compounds 2-(2,6-difluorophenyl)-4-(3xe2x80x2-chloro-4xe2x80x2-(1,1,2,2-tetrafluoroethoxy)-biphenyl-4)-2-oxazoline (EP-A-0 696 584) and 2-(2,6-difluorophenyl)-4-(3xe2x80x2-chloro-4xe2x80x2-methylbiphenyl-4)-2-oxazoline (EP-A-0 432 661).
However, the efficacy and/or the duration of action of these known compounds, in particular against certain organisms or at low application concentrations, is not entirely satisfactory in all areas of use.
This invention, accordingly, provides novel disubstituted biphenyloxazolines of the formula (I) 
in which
X1 represents hydrogen, halogen, alkyl, alkoxy or alkylthio,
X2 represents halogen, alkyl, alkoxy or alkylthio,
X3 represents hydrogen, halogen, alkyl, alkoxy or alkylthio, in particular hydrogen,
R1 represents hydrogen, halogen, alkyl or xe2x80x94CH2xe2x80x94CR4xe2x95x90CH2,
R2 represents alkyl, hydroxyalkyl, respectively optionally substituted alkenyl, alkinyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl, cycloalkenylalkyl, phenyl-alkyl, naphthylalkyl or tetrahydronaphthylalkyl and
R3 represents hydrogen, alkyl, halogen or the radical xe2x80x94CH2xe2x80x94CR4xe2x95x90CH2, where R1 and R3 do not simultaneously represent hydrogen, and
R4 represents hydrogen or respectively optionally substituted alkyl or aryl.
Owing to one or more chiral centres, the compounds of the formula (I) are generally obtained as stereoisomer mixtures. They can be employed both in the form of their diastereomer mixtures and as pure diastereomers or enantiomers.
Furthermore, it has been found that the novel compounds of the formula (I) are obtained when
A) compounds of the formula (II) 
xe2x80x83in which
X1, X2, X3, R3 and R1 are each as defined above, R3xe2x95x90R1=hydrogen being possible here if R2 represents allyl and step B) is carried out,
xe2x80x83are reacted with compounds of the formula (III)
Zxe2x80x94R2xe2x80x83xe2x80x83(III),
xe2x80x83in which
R2 is as defined above and
Z represents a leaving group,
xe2x80x83if appropriate in the presence of a diluent and if appropriate in the presence of a base and
B) if appropriate, the compounds of the formula (IV) obtained in this manner for R2xe2x95x90xe2x80x94CH2xe2x80x94CR4xe2x95x90CH2 and R3xe2x95x90H 
xe2x80x83in which
R1, R4, X1, X2 and X3 are each as defined above,
xe2x80x83are subsequently subjected to a Claisen rearrangement and
C) if appropriate, the resulting compounds of the formula (V) 
xe2x80x83in which
X1, X2, X3, R1 and R4 are each as defined above,
xe2x80x83are subsequently reacted with compounds of the formula (III)
Zxe2x80x94R2xe2x80x83xe2x80x83(III),
xe2x80x83in which
R2 and Z are each as defined above,
xe2x80x83if appropriate in the presence of a diluent and if appropriate in the presence of a base and,
if appropriate, steps B) and C) are then repeated for R2xe2x95x90xe2x80x94CH2xe2x80x94CR4xe2x95x90CH2 and R1xe2x95x90H, affording compounds of formula (Va) 
xe2x80x83in which
X1, X2, X3, R2 and R4 are each as defined above,
and the radicals R4 may be identical or different.
Furthermore, it has been found that the novel compounds of the formula (I) are highly suitable for controlling animal pests, in particular insects, arachnids and nematodes which are encountered in agriculture, in forests, in the protection of materials and of stored goods and in the hygiene sector.
The formula (I) provides a general definition of the compounds according to the invention.
Preferred substituents or ranges of the radicals listed in the formulae mentioned hereinabove and hereinbelow are illustrated below.
X1 preferably represents hydrogen, fluorine, chlorine, bromine, iodine, C1-C6-alkyl, C1-C6-alkoxy or C1-C6-alkylthio.
X2 preferably represents fluorine, chlorine, bromine, iodine, C1-C6-alkyl, C1-C6-alkoxy or C1-C6-alkylthio.
X3 preferably represents hydrogen, fluorine, chlorine, C1-C6-alkyl or C1-C6-alkoxy, in particular hydrogen.
R1 preferably represents hydrogen, fluorine, chlorine, bromine, C1-C6-alkyl or xe2x80x94CH2xe2x80x94CR4xe2x95x90CH2.
R2 preferably represents C1-C8-alkyl, C1-C6-hydroxyalkyl, C3-C10-alkenyl, C3-C12-alkinyl, preferably represents respectively optionally halogen- or C1-C4-alkyl-substituted C3-C6-cycloalkyl or C4-C6-cycloalkenyl,
preferably represents optionally halogen-, C1-C4-alkyl-, C2-C4-alkenyl-, C2-C4-halogenoalkenyl-, phenyl-, halogenophenyl-, styryl- or halogenostyryl-substituted C3-C6-cycloalkyl-C1-C4-alkyl,
preferably represents optionally halogen- or C1-C4-alkyl-substituted C4-C8-cycloalkenyl-C1-C2-alkyl,
or preferably represents phenyl-C1-C4-alkyl which is optionally mono- to tetrasubstituted by identical or different substituents from the group consisting of nitro, halogen, C1-C12-alkyl, C1-C12-halogenoalkyl, C1-C12-alkylthio, C1-C12-halogenoalkylthio, C1-C12-alkoxy and C1-C12-halogenoalkoxy, preferably represents naphthyl-C1-C3-alkyl or tetrahydronaphthyl-C1-C3-alkyl.
R3 preferably represents hydrogen, C1-C4-alkyl, fluorine, chlorine, bromine or represents xe2x80x94CH2xe2x80x94CR4xe2x95x90CH2, where R1and R3 do not simultaneously represent hydrogen.
R4 preferably represents hydrogen, C1-C12-alkyl or preferably represents phenyl which is optionally mono- to tetrasubstituted by identical or different substituents from the group consisting of halogen, C1-C12-alkyl, C1-C12-halogenoalkyl, C1-C12-alkoxy and C1-C12-halogenoalkoxy.
X1 particularly preferably represents hydrogen, fluorine or chlorine.
X2 particularly preferably represents fluorine, chlorine, bromine, iodine, C1-C3-alkyl or C1-C3-alkoxy.
X3 particularly preferably represents hydrogen, fluorine, chlorine, C1-C3-alkyl or C1-C3-alkoxy, in particular hydrogen.
R1 particularly preferably represents hydrogen, fluorine, chlorine, bromine, C1-C4-alkyl or xe2x80x94CH2xe2x80x94CR4xe2x95x90CH2.
R2 particularly preferably represents C1-C6-alkyl, C1-C4-hydroxyalkyl, C3-C10-alkenyl, C3-C5-alkinyl, particularly preferably represents respectively optionally halogen- or C1-C4-alkyl-substituted cyclohexyl or C4-C6-cycloalkenyl,
particularly preferably represents optionally halogen-, C1C4-alkyl-, C2-C4-alkenyl-, C2-C3-halogenoalkenyl-, phenyl-, halogenophenyl-, styryl- or halogenostyryl-substituted C3-C6-cycloalkyl-C1-C4-alkyl,
particularly preferably represents optionally halogen-substituted C4-C6-cycloalkenylmethyl or
particularly preferably represents benzyl which is optionally mono- or disubstituted by identical or different substituents from the group consisting of nitro, halogen, C1-C4-alkyl, C1-C4-halogenoalkyl, C1-C4-alkylthio,
C1-C4-halogenoalkylthio, C1-C4-alkoxy and C1-C4-halogenoalkoxy, particularly preferably represents naphthylmethyl or tetrahydronaphthyl-methyl.
R3 particularly preferably represents hydrogen, C1-C3-alkyl, chlorine, bromine or xe2x80x94CH2xe2x80x94CR4xe2x95x90CH2, where R1 and R3 do not simultaneously represent hydrogen.
R4 particularly preferably represents hydrogen, C1-C4-alkyl or particularly preferably represents phenyl which is optionally mono- or disubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine, C1-C4-alkyl, C1-C4-halogenoalkyl and C1-C4-halogenoalkoxy.
In the preferred and particularly preferred radical definitions, halogen represents in particular fluorine, chlorine and bromine.
X1 very particularly preferably represents hydrogen, fluorine or chlorine.
X2 very particularly preferably represents fluorine, chlorine, bromine, iodine, methyl or methoxy.
X3 very particularly preferably represents hydrogen, fluorine, chlorine or methyl, in particular hydrogen.
R1 very particularly preferably represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl or represents allyl.
R2 very particularly preferably represents methyl, ethyl, n- or i-propyl, n-butyl, i-butyl, s-butyl, n-pentyl, n-hexyl, hydroxyethyl, hydroxypropyl, hydroxybutyl, very particularly preferably represents xe2x80x94CH2xe2x80x94CHxe2x95x90CH2, xe2x80x94CH2xe2x80x94C(CH3)xe2x95x90CH2, xe2x80x94CH2xe2x80x94Cxe2x89xa1CH or xe2x80x94CH(CH3)Cxe2x89xa1CH,
very particularly preferably represents one of the cycloalkylalkyl groupings: 
very particularly preferably represents, 
very particularly preferably represents 
very particularly preferably represents one of the radicals below: 
R3 very particularly preferably represents hydrogen, chlorine, bromine, methyl or xe2x80x94CH2xe2x80x94CHxe2x95x90CH2, in particular hydrogen, chlorine or xe2x80x94CH2xe2x80x94CHxe2x95x90CH2, where R1 and R3 do not simultaneously represent hydrogen.
Preference is furthermore given to compounds of the formula (Ia) 
in which
R1, R2, R3, X1 and X2 each have the abovementioned general, preferred, particularly preferred or very particularly preferred meanings.
In each case, R1 and R3 may not simultaneously represent hydrogen.
A preferred group of compounds are also those compounds of the formula (Ib) 
in which
X1 represents hydrogen or fluorine,
X2 represents fluorine, chlorine, bromine or methyl,
R1represents chlorine, methyl, ethyl, n- or i-propyl or allyl and
R2 has the abovementioned general, preferred, particularly preferred and very particularly preferred meanings and most preferably represents benzyl which may be substituted as mentioned above,
R3 represents hydrogen, chlorine, bromine, methyl or allyl, in particular hydrogen, chlorine or allyl.
Within these groups, preference is given to compounds in which R3 represents hydrogen.
The hydrocarbon radicals, such as alkyl or alkenyl, mentioned above in the definition of the compounds according to the invention arexe2x80x94also in combination with hetero atoms, such as in alkoxyxe2x80x94in each case straight-chain or branched as far as this is possible.
The abovementioned general or preferred definitions of radicals or illustrations can be combined with one another as desired, that is to say combinations between the respective ranges and preferred ranges are also possible. They apply both to the end products and, correspondingly, to the precursors and intermediates.
Preference according to the invention is given to those compounds of the formula (I) which contain a combination of the definitions given above as being preferred (preferable).
Particular preference according to the invention is given to those compounds of the formula (I) which contain a combination of the definitions given above as being particularly preferred.
Very particular preference according to the invention is given to those compounds of the formula (I) which contain a combination of the definitions given above as being very particularly preferred.
Using, for example, 2-(2,6-difluorophenyl)-4-(4xe2x80x2-hydroxy-3xe2x80x2-n-propylbiphenyl-4)-2-oxazoline and isopropyl bromide as starting materials, the course of step A) of the process according to the invention can be represented by the following equation: 
Using, for example, 2-(2,6-difluorophenyl)-4-(4xe2x80x2-allyloxy-3xe2x80x2-chlorobiphenyl-4)-2-oxazoline as starting material, the course of step B) of the process according to the invention can be represented by the following equation: 
Using, for example, 2-(2,6-difluorophenyl)-4-(3xe2x80x2-allyl-5xe2x80x2-chloro-4xe2x80x2-hydroxybiphenyl-4)-2-oxazoline and benzyl bromide as starting materials, the course of step C) of the process according to the invention can be represented by the following equation: 
The compounds of the formula (II) required as starting materials for step A) of the process according to the invention are novel if R3 and R1do not simultaneously represent hydrogen.
The compounds of the formula (II) are obtained, for example, when compounds of the formula (VI) 
in which
X1, X2, X3, R1 and R3 are each as defined above and
R5 represents alkyl (for example methyl), aryl (for example phenyl) or alkoxy (for example methoxy or ethoxy), are cyclized in the presence of a base, if appropriate in the presence of a catalyst and if appropriate in the presence of a diluent, and the acyl group is subsequently cleaved off (process D).
Using, for example, 2,6-difluoro-N-[2-chloro-1-(4-(4-acetoxy-3-n-propyl-phenyl)phenyl)ethyl]-benzamide as starting material, the course of the process D) for preparing compounds of the formula (II) can be represented by the following equation: 
Suitable diluents for process D) are all inert organic solvents. If appropriate, they can be employed as a mixture with water. Preference is given to using hydrocarbons such as toluene, xylene, tetralin, hexane, cyclohexane, halogenated hydrocarbons such as methylene chloride, chloroform, chlorobenzene, o-dichlorobenzene, alcohols such as methanol, ethanol, glycol, the isomeric propanols, butanols, pentanols, ethers such as diethyl ether, diisopropyl ether, dimethoxyethane, tetrahydro furan, dioxane, nitriles such as acetonitrile or butyronitrile, amides such as dimethylformamide, sulphoxides such as dimethyl sulphoxide, and furthermore sulpholane. Particular preference is given to using alcohols or dimethylformamide.
Suitable bases for the cyclization are all customary acid acceptors.
Preference is given to using tertiary amines such as triethylamine, pyridine, DABCO, DBU, DBN, N,N-dimethylaniline, furthermore alkaline earth metal oxides such as magnesium oxide and calcium oxide, additionally alkali metal carbonates and alkaline earth metal carbonates such as sodium carbonate, potassium carbonate and calcium carbonate, alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, and furthermore alkoxides such as sodium ethoxide or potassium tert-butoxide.
If appropriate, the reaction is carried out in the presence of a phase transfer catalyst. Suitable phase transfer catalysts are for example ammonium compounds such as tetraoctylammonium bromide or benzyltriethylammonium chloride.
The reaction temperature can be varied within a relatively wide range. In general, the reaction is carried out at temperatures between xe2x88x9220xc2x0 C. and 150xc2x0 C., preferably between xe2x88x9210xc2x0 C. and 100xc2x0 C.
The reaction is generally carried out under atmospheric pressure.
In general, an equimolar amount of base is employed. However, it is also possible to use an excess of base.
Preferred diluents for the subsequent hydrolysis are water/alcohol mixtures such as, for example, water/methanol, water/ethanol or water/propanol or water/amide mixtures such as, for example, water/dimethylformamide (DMF) or water/dimethyl-acetamide.
The hydrolysis is carried out in the presence of a base. Suitable bases include inorganic and organic bases, in particular alkali metal hydroxides such as sodium hydroxide or potassium hydroxide or ammonia.
For the hydrolysis, the reaction temperature can be varied within a relatively wide range. In general, the reaction is carried out at temperatures between xe2x88x9210xc2x0 C. and 60xc2x0 C., preferably between 0xc2x0 C. and 40xc2x0 C. The reaction is generally carried out under atmospheric pressure.
The cyclization and the removal of the acyl groups can be carried out both as a onepot reaction and in two separate steps.
The compounds of the formula (VI) required as starting materials for the process D) are novel.
The compounds of the formula (VI) are obtained, for example, when compounds of the formula (VII) 
in which
R1, R3 and R5 are each as defined above
are reacted with compounds of the formula (VIII) 
in which
X1, X2 and X3 are each as defined above
in the presence of an acid catalyst, for example a Lewis acid such as iron(III) chloride, aluminium chloride or hydrogen fluoride and preferably in the presence of a diluent, for example a halogenated, in particular chlorinated, hydrocarbon such as dichloromethane, at temperatures between xe2x88x9220xc2x0 C. and 80xc2x0 C. (cf. the Preparation Examples and also WO 96/18619).
Some of the compounds of the formula (VII) are known (J. Amer Chem. Soc. 61, 1447, 3037 (1939); J. Amer. Chem. Soc. 56, 202 (1934); J. Amer. Chem. Soc. 64, 2219 (1942); J. Amer. Chem. Soc. 89, 2711 (1967); J. Org. Chem. 27, 2671 (1962); J. Indian Chem. Soc. 12, 410 (1935); DE-1 911 520) or can be prepared by known methods, for example by reaction of the corresponding hydroxybiphenyls of the formula (IX) with the acid anhydrides of the formula (X) or the acyl halides (in particular acyl chlorides) of the formula (XI): 
Some of the compounds of the formula (IX) are known (see for example J.Org.Chem. 29, 2640 (1964), J. Indian Chem. Soc. 12, 410 (1935), J. Amer. Chem. Soc. 80 3271 (1958), J. Amer. Soc. 56, 202 (1934), J. Org. Chem. 29, 3014 (1964)) or can be prepared by known methods (cf. the Preparation Examples), for example in the following way, 
the starting material being known from Bull. Chem. Soc. Jap. 56, 2037 (1983), or according to 
the starting material being known (see J. Amer. Chem. Soc. 80, 3271, (1958)).
The compounds of the formulae (X) and (XI) are generally known and in many cases commercially available or obtainable from the corresponding carboxylic acids in a simple and known manner.
The compounds of the formula (VIII) are known (see for example EP-A-0 594 179, WO 96/18619), or they can be prepared by the methods described therein.
The compounds of the formula (VI) can also be obtained when acyl chlorides of the formula (XII) 
in which
X1, X2 and X3 are each as defined above
are reacted with amino alcohols of the formula (XIII) 
in which
R1 and R3 are each as defined above,
if appropriate in the presence of a diluent (suitable diluents are all solvents which are inert towards these compounds; preference is given to using hydrocarbons, such as benzine, benzene, toluene, xylene and tetralin, furthermore halogenated hydrocarbons, such as methylene chloride, chloroform, carbon tetrachloride, chlorobenzene and o-dichlorobenzene, additionally ketones, such as acetone and methyl isopropyl ketone, furthermore ethers, such as diethyl ether, tetrahydrofuran and dioxane, additionally carboxylic esters, such as ethyl acetate, and also strongly polar solvents, such as dimethyl sulphoxide and sulpholane; the hydrolytic stability of the acyl halide permitting, the reaction can also be carried out in the presence of water) and, if appropriate, in the presence of a base (suitable bases for the reaction are all customary acid acceptors, preference being given to using tertiary amines, such as triethylamine, pyridine, diazabicyclooctane (DABCO), diazabicycloundecene (DBU), diazabicyclononene (DBN), Hxc3xcnig base and N,N-dimethyl-aniline, furthermore alkaline earth metal oxides, such as magnesium oxide and calcium oxide, additionally alkali metal carbonates and alkaline earth metal carbonates, such as sodium carbonate, potassium carbonate and calcium carbonate and alkali metal hydroxides or alkaline earth metal hydroxides such as sodium hydroxide or potassium hydroxide), at temperatures between xe2x88x9220xc2x0 C. and +100xc2x0 C., preferably between 0xc2x0 C. and 30xc2x0 C., and, if appropriate, the resulting compounds of the formula (XIV) 
in which
X1, X2, X3, R3 and R1 are each as defined above
are then reacted with a chlorinating agent such as thionyl chloride, phosgene or phosphorus oxychloride, if appropriate in the presence of a diluent, for example hydrocarbons such as toluene, xylene, hexane, cyclohexane, halogenated hydrocarbon such as chlorobenzene, chloroform, methylene chloride or ethers such as diethyl ether, diisopropyl ether, dimethoxyethane, tetrahydrofuran or dioxane, at temperatures between 0xc2x0 C. and 120xc2x0 C., preferably between 20xc2x0 C. and 100xc2x0 C. (cf. EP-A-0 696 584).
The compounds of the formula (XII) are generally known and in many cases commercially available or obtainable from the corresponding carboxylic acids in a simple and known manner.
The compounds (XIII) are known (cf. EP-A-0 696 584) or can be prepared by methods described therein.
The compounds of the formula (III) furthermore required as starting materials in step A) of the process according to the invention are generally known compounds of organic chemistry. Z represents a customary leaving group, for example halogen (in particular chlorine or bromine), alkylsulphonyloxy (in particular methylsulphonyloxy) or optionally substituted arylsulphonyloxy (in particular phenylsulphonyloxy, p-cholorophenylsulphonyloxy or tolylsulphonyloxy).
Step A) of the process according to the invention is characterized in that a compound of the formula (II) is reacted with a compound of the formula (III), if appropriate in the presence of a diluent and if appropriate in the presence of a base.
Suitable diluents are all customary solvents. Preference is given to using optionally halogenated, aromatic or aliphatic hydrocarbons, ketones, nitrites and amides. Examples include toluene, acetone, acetonitrile, dimethylformamide and dimethylacetamide.
Suitable bases are all customary inorganic and organic bases. Examples include tertiary amines such as triethylamine, DBN, DBU, DABCO, alkali metal hydroxides and alkaline earth metal hydroxides such as, for example, sodium hydroxide, potassium hydroxide and calcium hydroxide, and alkali metal carbonates and alkaline earth metal carbonates such as, for example, sodium carbonate or potassium carbonate.
The reaction temperature can be varied within a relatively wide range. In general, the reaction is carried out at temperatures between xe2x88x9220xc2x0 C. and 100xc2x0 C., preferably between 0xc2x0 C. and 60xc2x0 C.
The reaction is generally carried out under atmospheric pressure.
The compounds of the formula (II) and the compounds of the formula (III) are generally employed in approximately equimolar amounts. However, it is also possible to employ an excess of the compounds of the formula (III).
Step B) of the process according to the invention is characterized in that compounds of the formula (IV) are subjected to a Claisen rearrangement.
For this purpose, the compounds of the formula (IV) are heated, neat or in the presence of a diluent (chlorobenzene, dichlorobenzene, diethylaniline), to temperatures of from 160xc2x0 C. to 290xc2x0 C., preferably 180xc2x0 C. to 260xc2x0 C. (see also D. S. Tarbell, The Claisen Rearrangement, Org. Reactions 2, 1 ff (1944)).
Step C) of the process according to the invention is characterized in that compounds of the formula (V) are reacted with compounds of the formula (III), if appropriate in the presence of a diluent and if appropriate in the presence of a base.
For this reaction, which is similar to step A), what has been said for step A) with respect to diluent, base, reaction temperature, etc., also applies.
The active compounds are suitable for controlling animal pests, in particular insects, arachnids and nematodes, encountered in agriculture, in forestry, in the protection of stored products and of materials, and in the hygiene sector, and have good plant safety and low toxicity to warm-blooded animals. They are active against normally sensitive and resistant species and against all or some stages of development. The abovementioned pests include:
From the order of the Isopoda, for example, Oniscus asellus, Armadillidium vulgare and Porcellio scaber. 
From the order of the Diplopoda, for example, Blaniulus guttulatus. 
From the order of the Chilopoda, for example, Geophilus carpophagus and Scutigera spec.
From the order of the Symphyla, for example, Scutigerella immaculata. 
From the order of the Thysanura, for example, Lepisma saccharina. 
From the order of the Collembola, for example, Onychiurus armatus. 
From the order of the Orthoptera, for example, Blatta orientalis, Periplaneta americana, Leucophaea maderae, Blattella germanica, Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus differentialis and Schistocerca gregaria. 
From the order of the Dermaptera, for example, Forficula auricularia. 
From the order of the Isoptera, for example, Reticulitermes spp.
From the order of the Anoplura, for example, Pediculus humanus corporis, Haematopinus spp. and Linognathus spp.
From the order of the Mallophaga, for example, Trichodectes spp. and Damalinea spp.
From the order of the Thysanoptera, for example, Hercinothrips femoralis and Thrips tabaci. 
From the order of the Heteroptera, for example, Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus and Triatoma spp.
From the order of the Homoptera, for example, Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Aphis pormi, Eriosoma lanigerum, Hyalopterus arundinis, Phylloxera vastatrix, Pemphigus spp., Macrosiphum avenae, Myzus spp., Phorodon humuli, Rhopalosiphum padi, Empoasca spp., Euscelis bilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp. and Psylla spp.
From the order of the Lepidoptera, for example, Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella maculipennis, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp., Bucculatrix thurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltia spp., Earias insulana, Heliothis spp., Laphygma exigua, Mamestra brassicae, Panolis flammea, Prodenia litura, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleria mellonella, Tineola bisselliella, Tinea pellionella, Hofinannophila pseudospretella, Cacoecia podana, Capua reticulana, Choristoneura fumiferana, Clysia ambiguella, Homona magnanima and Tortrix viridana. 
From the order of the Coleoptera, for example, Anobium punctaturn, Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus, Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedon cochleariae, Diabrotica spp., Psylliodes chrysocephala, Epilachna varivestis, Atomaria spp., Oryzaephilus surinamensis, Anthonomus spp., Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus, Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogoderma spp., Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp., Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha, Amphimallon solstitialis and Costelytra zealandica. 
From the order of the Hymenoptera, for example, Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis and Vespa spp.
From the order of the Diptera, for example, Aedes spp., Anopheles spp., Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphora erythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp., Gastrophilus spp., Hyppobosca spp., Stomoxys spp., Oestrus spp., Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae and Tipula paludosa. 
From the order of the Siphonaptera, for example, Xenopsylla cheopis and Ceratophyllus spp.
From the order of the Arachnida, for example, Scorpio maurus and Latrodectus mactans. 
From the order of the Acarina, for example, Acarus siro, Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp. and Tetranychus spp.
The phytoparasitic nematodes include Pratylenchus spp., Radopholus similis, Ditylenchus dipsaci, Tylenchulus semipenetrans, Heterodera spp., Meloidogyne spp., Aphelenchoides spp., Longidorus spp., Xiphinema spp. and Trichodorus spp.
The compounds of the formula (I) according to the invention in particular have outstanding insecticidal and acaricidal activity.
They are particularly successfully used for controlling plant-damaging insects, for example against mustard beetle larvae (Phaedon cochleariae), caterpillars of the owlet moth (Spodoptera frugiperda), and green peach aphids (Myzus persicae) or for controlling plant-damaging mites, for example against the greenhouse red spider mite (Tetranychus urticae).
The active compounds can be converted to the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusting agents, pastes, soluble powders, granules, suspoemulsion concentrates, natural and synthetic materials impregnated with active compound and very fine capsules in polymeric substances.
These formulations are produced in a known manner, for example by mixing the active compounds with extenders, that is liquid solvents and/or solid carriers, if appropriate with the use of surfactants, that is emulsifiers and/or dispersants and/or foam-formers.
If the extender used is water, it is also possible to use, for example, organic solvents as auxiliary solvents. Suitable liquid solvents are essentially: aromatics, such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example mineral oil fractions, mineral and vegetable oils, alcohols, such as butanol or glycol and their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethylformamide and dimethyl sulphoxide, and water.
Suitable solid carriers are: for example ammonium salts and ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as finely divided silica, alumina and silicates; suitable solid carriers for granules are: for example crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite, and synthetic granules of inorganic and organic meals, and granules of organic material such as sawdust, coconut shells, maize cobs and tobacco stalks; suitable emulsifiers and/or foam-formers are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonates and protein hydrolysates; suitable dispersants are: for example lignin-sulphite waste liquors and methylcellulose.
Tackifiers such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, and natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids, can be used in the formulations. Other additives can be mineral and vegetable oils.
It is possible to use colorants such as inorganic pigments, for example iron oxide, titanium oxide and Prussian Blue, and organic dyestuffs, such as alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs, and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
The formulations in general contain between 0.1 and 95% by weight of active compound, preferably between 0.5 and 90%, and preferably in addition extenders and/or surfactants.
The active compound according to the invention can be present in its commercially available formulations and in the use forms, prepared from these formulations, as a mixture with other active compounds, such as insecticides, attractants, sterilizing agents, bactericides, acaricides, nematicides, fungicides, growth-regulating substances or herbicides. The insecticides include, for example, phosphates, carbamates, carboxylates, chlorinated hydrocarbons, phenylureas and substances produced by microorganisms, inter alia.
Examples of particularly advantageous mixing components are the following:
Fungicides
2-aminobutane; 2-anilino-4-methyl-6-cyclopropyl-pyrimidine; 2xe2x80x2,6xe2x80x2-dibromo-2-methyl-4xe2x80x2-trifluoromethoxy-4xe2x80x2-trifluoro-methyl-1,3-thiazole-5-carboxanilide; 2,6-dichloro-N-(4-trifluoromethylbenzyl)-benzamide; (E)-2-methoxyimino-N-methyl-2-(2-phenoxyphenyl)-acetamide; 8-hydroxyquinoline sulphate; methyl (E)-2-{2-[6-(2-cyanophenoxy)-pyrimidin-4-yloxy]-phenyl}-3-methoxyacrylate; methyl (E)-methoximino[alpha-(o-tolyloxy)-o-tolyl]acetate; 2-phenylphenol (OPP), aldimorph, ampropylfos, anilazine, azaconazole,
benalaxyl, benodanil, benomyl, binapacryl, biphenyl, bitertanol, blasticidin-S, bromuconazole, bupirimate, buthiobate,
calcium polysulphide, captafol, captan, carbendazim, carboxin, quinomethionate, chloroneb, chloropicrin, chlorothalonil, chlozolinate, cufraneb, cymoxanil, cyproconazole, cyprofuram,
dichlorophen, diclobutrazol, diclofluanid, diclomezine, dicloran, diethofencarb, difenoconazole, dimethirimol, dimethomorph, diniconazole, dinocap, diphenylamine, dipyrithione, ditalimfos, dithianon, dodine, drazoxolon,
edifenphos, epoxyconazole, ethirimol, etridiazole,
fenarimol, fenbuconazole, fenfuram, fenitropan, fenpiclonil, fenpropidin, fenpropimorph, fentin acetate, fentin hydroxide, ferbam, ferimzone, fluazinam, fludioxonil, fluoromide, fluquinconazole, flusilazole, flusulfamide, flutolanil, flutriafol, folpet, fosetyl-aluminium, fthalide, fuberidazole, furalaxyl, furmecyclox,
guazatine,
hexachlorobenzene, hexaconazole, hymexazol,
imazalil, imibenconazole, iminoctadine, iprobenfos (IBP), iprodione, isoprothiolane,
kasugamycin, copper preparations such as: copper hydroxide, copper naphthenate, copper oxychloride, copper sulphate, copper oxide, oxine-copper and Bordeaux mixture,
mancopper, mancozeb, maneb, mepanipyrim, mepronil, metalaxyl, metconazole, methasulfocarb, methfuroxam, metiram, metsulfovax, myclobutanil,
nickel dimethyldithiocarbamate, nitrothal-isopropyl, nuarimol,
ofurace, oxadixyl, oxamocarb, oxycarboxin,
pefurazoate, penconazole, pencycuron, phosdiphen, phthalide, pimaricin, piperalin, polycarbamate, polyoxin, probenazole, prochloraz, procymidone, propamocarb, propiconazole, propineb, pyrazophos, pyrifenox, pyrimethanil, pyroquilon,
quintozene (PCNB),
sulphur and sulphur preparations,
tebuconazole, tecloftalam, tecnazene, tetraconazole, thiabendazole, thicyofen, thiophanatemethyl, thiram, tolclofos-methyl, tolylfluanid, triadimefon, triadimenol, triazoxide, trichlamide, tricyclazole, tridemorph, triflumizole, triforine, triticonazole,
validamycin A, vinclozolin,
zineb, ziram.
Bactericides
bronopol, dichlorophen, nitrapyrin, nickel dimethyldithiocarbamate, kasugamycin, octhilinone, furancarboxylic acid, oxytetracycline, probenazole, streptomycin, tecloftalam,
copper sulphate and other copper preparations.
Insecticides/Acaricides/Nematicides
abamectin, AC 303 630, acephate, acrinathrin, alanycarb, aldicarb, alphamethrin, amitraz, avermectin, AZ 60541, azadirachtin, azinphos A, azinphos M, azocyclotin,
bacillus thuringiensis, bendiocarb, benfuracarb, bensultap, beta-cyfluthrin, bifenthrin, BPMC, brofenprox, bromophos A, bufencarb, buprofezin, butocarboxim, butylpyridaben,
cadusafos, carbaryl, carbofuran, carbophenothion, carbosulfan, cartap, CGA 157419, CGA 184699, chloethocarb, chlorethoxyfos, chlorfenvinphos, chlorfluazuron, chlormephos, chlorpyrifos, chlorpyrifos M, cis-resmethrin, clocythrin, clofentezine, cyanophos, cycloprothrin, cyfluthrin, cyhalothrin, cyhexatin, cypermethrin, cyromazine,
deltamethrin, demeton M, demeton S, demeton-S-methyl, diafenthiuron, diazinon, dichlofenthion, dichlorvos, dicliphos, dicrotophos, diethion, diflubenzuron, dimethoate, dimethylvinphos, dioxathion, disulfoton,
edifenphos, emamectin, esfenvalerate, ethiofencarb, ethion, ethofenprox, ethoprophos, etrimfos,
fenamiphos, fenazaquin, fenbutatin oxide, fenitrothion, fenobucarb, fenothiocarb, fenoxycarb, fenpropathrin, fenpyrad, fenpyroximate, fenthion, fenvalerate, fipronil, fluazinam, flucycloxuron, flucythrinate, flufenoxuron, flufenprox, fluvalinate, fonofos, formothion, fosthiazate, fubfenprox, furathiocarb,
HCH, heptenophos, hexaflumuron, hexythiazox,
imidacloprid, iprobenfos, isazofos, isofenphos, isoprocarb, isoxathion, ivermectin,
lambda-cyhalothrin, lufenuron,
malathion, mecarbam, mervinphos, mesulfenphos, metaldehyde, methacrifos, methamidophos, methidathion, methiocarb, methomyl, metolcarb, milbemectin, monocrotophos, moxidectin,
naled, NC 184, NI 25, nitenpyram,
omethoate, oxamyl, oxydemethon M, oxydeprofos,
parathion A, parathion M, permethrin, phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim, pirimicarb, pirimiphos M, pirimiphos A, profenofos, promecarb, propaphos, propoxur, prothiofos, prothoate, pymetrozine, pyrachlophos, pyridaphenthion, pyresmethrin, pyrethrum, pyridaben, pyrimidifen, pyriproxyfen,
quinalphos,
RH 5992,
salithion, sebufos, silafluofen, sulfotep, sulprofos,
tebufenozide, tebufenpyrad, tebupirimphos, teflubenzuron, tefluthrin, temephos, terbam, terbufos, tetrachlorvinphos, thiafenox, thiodicarb, thiofanox, thiomethon, thionazin, thuringiensin, tralomethrin, triarathene, triazophos, triazuron, trichlorfon, triflumuron, trimethacarb,
vamidothion, XMC, xylylcarb, YI 5301/5302, zetamethrin.
A mixture with other known active compounds, such as herbicides, or with fertilizers and growth-regulators is also possible.
The active compounds according to the invention can furthermore be present in their commercially available formulations and in the use forms, prepared from these formulations, as a mixture with synergistic agents. Synergistic agents are compounds which increase the action of the active compounds, without it being necessary for the synergistic agent added to be active itself.
The active compound content of the use forms prepared from the commercially available formulations can vary within wide limits. The active compound concentration of the use forms can be from 0.0000001 to 95% by weight of active compound, preferably between 0.0001 and 1% by weight.
The compounds are employed in a customary manner appropriate for the use forms.
When used against hygiene and stored-product pests, the active compound has an excellent residual action on wood and clay as well as a good stability to alkali on limed substrates.
The active compounds according to the invention are not only active against plant, hygiene and stored-product pests, but also, in the veterinary medicine sector, against animal parasites (ectoparasites), such as ixodid ticks, argasid ticks, scab mites, trombiculid mites, flies (stinging and sucking), parasitic fly larvae, lice, hair lice, bird lice and fleas. These parasites include:
From the order of the Anoplurida, for example, Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp. and Solenopotes spp.
From the order of the Mallophagida and the sub-orders Amblycerina and Ischnocerina, for example, Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp., Trichodectes spp. and Felicola spp.
From the order of the Diptera and the sub-orders Nematocerina and Brachycerina, for example, Aedes spp., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp., Chrysops spp., Hybomitra spp., Atylotus spp., Tabanus spp., Haematopota spp., Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fannia spp., Glossina spp., Calliphora spp., Lucilia spp., Chrysomyia spp., Wohlfahrtia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp., Gasterophilus spp., Hippobosca spp., Lipoptena spp. and Melophagus spp.
From the order of the Siphonapterida, for example, Pulex spp., Ctenocephalides spp., Xenopyslla spp. and Ceratophyllus spp.
From the order of the Heteropterida, for example, Cimex spp., Triatoma spp., Rhodnius spp. and Panstrongylus spp.
From the order of the Blattarida, for example, Blatta orientalis, Periplaneta americana, Blattela germanica and Supella spp.
From the sub-class of the Acaria (Acarida) and the orders of the Meta- and Mesostigmata, for example, Argas spp., Ornithodorus spp., Otabius spp., Ixodes spp., Amblyomma spp., Boophilus spp., Dermacentor spp., Haemophysalis spp., Hyalomma spp., Rhipicephalus spp., Dermanyssus spp., Raillietia spp., Pneumonyssus spp., Stemostoma spp. and Varroa spp.
From the order of the Actinedida (Prostigmata) and Acaridida (Astigmata), for example, Acarapis spp., Cheyletiella spp., Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp. and Laminosioptes spp.
For example, they have a good development-inhibitory activity against Lucilia cuprina fly larvae.
The active compounds of the formula (I) according to the invention are also suitable for controlling arthropods which attack agricultural livestock, such as, for example, cattle, sheep, goats, horses, pigs, donkeys, camels, buffalo, rabbits, chickens, turkeys, ducks, geese, honey bees, other domestic animals, such as, for example, dogs, cats, caged birds, aquarium fish, and so-called experimental animals, such as, for example, hamsters, guineapigs, rats and mice. By controlling these arthropods, it is intended to reduce deaths and decreased performances (in meat, milk, wool, hides, eggs, honey and the like), so that more economical and simpler animal keeping is made possible by using the active compounds according to the invention.
In the veterinary sector, the active compounds according to the invention are used in a known manner by enteral administration, for example in the form of tablets, capsules, drinks, drenches, granules, pastes, boluses, the feed-through method, suppositories, by parenteral administration, such as, for example, by means of injections (intramuscular, subcutaneous, intravenous, intraperitoneal and the like), implants, by nasal administration, by dermal administration, for example in the form of dipping or bathing, spraying, pouring-on and spotting-on, washing, dusting, and with the aid of shaped articles which comprise active compound, such as collars, ear tags, tail marks, limb bands, halters, marking devices and the like.
When administered to livestock, poultry, domestic animals and the like, the active compounds of the formula (I) can be used as formulations (for example powders, emulsions, flowables) which comprise the active compounds in an amount of 1 to 80% by weight, either directly or after dilution by a factor of 100 to 10,000, or they may be used in the form of a chemical bath.
Furthermore, it has been found that the compounds of the formula (I) according to the invention have a potent insecticidal action against insects which destroy industrial materials.
The following insects may be mentioned by way of preferred examples but without any limitation:
Beetles, such as Hylotrupes bajulus, Chlorophorus pilosis, Anobium punctatum, Xestobium rufovillosum, Ptilinus pecticornis, Dendrobium pertinex, Ernobius mollis, Priobium carpini, Lyctus brunneus, Lyctus africanus, Lyctus planicollis, Lyctus linearis, Lyctus pubescens, Trogoxylon aequale, Minthes rugicollis, Xyleborus spec. Tryptodendron spec., Apate monachus, Bostrychus capucins, Heterobostrychus brunneus, Sinoxylon spec. Dinoderus minutus. 
Dermapterans, such as Sirex juvencus, Urocerus gigas, Urocerus gigas taignus and Urocerus augur. 
Termites, such as Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicola, Reticulitermes flavipes, Reticulitermes santonensis, Reticulitermes lucifugus, Mastotermes darwiniensis, Zootermopsis nevadensis and Coptotermes formosanus. 
Bristletails, such as Lepisma saccharina. 
Industrial materials are to be understood as meaning, in the present context, non-live materials, such as, preferably, synthetic materials, glues, sizes, paper and board, leather, wood and timber products, and paint.
The materials to be very particularly preferably protected against attack by insects are wood and timber products.
Wood and timber products which can be protected by the composition according to the invention or mixtures comprising such a composition are to be understood as meaning, for example, construction timber, wooden beams, railway sleepers, bridge components, jetties, wooden vehicles, boxes, pallets, containers, telephone poles, wood lagging, windows and doors made of wood, plywood, particle board, joiner""s articles, or wood products which, quite generally, are used in the construction of houses or in joinery.
The active compounds can be used as such, in the form of concentrates or generally customary formulations, such as powders, granules, solutions, suspensions, emulsions or pastes.
The formulations mentioned can be prepared in a manner known per se, for example by mixing the active compounds with at least one solvent or diluent, emulsifier, dispersant and/or binder or fixative, water repellant, if appropriate desiccants and UV stabilizers and, if appropriate, colorants and pigments and other processing auxiliaries.
The insecticidal compositions or concentrates used for the protection of wood and wooden materials comprise the active compound according to the invention at a concentration of 0.0001 to 95% by weight, in particular 0.001 to 60% by weight.
The amount of the compositions or concentrates employed depends on the species and the occurrence of the insects and on the medium. The optimum rate of application can be determined upon use in each case by test series. However, in general, it suffices to employ 0.0001 to 20% by weight, preferably 0.001 to 10% by weight, of the active compound, based on the material to be protected.
The solvent and/or diluent used is an organochemical solvent or solvent mixture and/or an oily or oil-type organochemical solvent or solvent mixture of low volatility and/or a polar organochemical solvent or solvent mixture and/or water and, if appropriate, an emulsifier and/or wetting agent.
Organochemical solvents which are preferably employed are oily or oil-like solvents having an evaporation number of above 35 and a flashpoint of above 30 C., preferably above 45 C.; Substances which are used as such oily and oil-like solvents which have low volatility and are insoluble in water are suitable mineral oils or their aromatic fractions, or mineral-oil-containing solvent mixtures, preferably white spirit, petroleum and/or alkyl-benzene.
Substances which are advantageously used are mineral oils with a boiling range of 170 to 220 C., white spirit with a boiling range of 170 to 220 C., spindle oil with a boiling range of 250 to 350 C., petroleum or aromatics of boiling range of 160 to 280 C., essence of turpentine and the like.
In a preferred embodiment, liquid aliphatic hydrocarbons with a boiling range of 180 to 210 C. or high-boiling mixtures of aromatic and aliphatic hydrocarbons with a boiling range of 180 to 220 C. and/or spindle oil and/or monochloronaphthalene, preferably ∀-monochloronaphthalene, are used.
The organic oily or oil-like solvents of low volatility and having an evaporation number of above 35 and a flashpoint of above 30 C., preferably above 45 C., can be partially replaced by organochemical solvents of high or medium volatility, with the proviso that the solvent mixture also has an evaporation number of above 35 and a flashpoint of above 30 C., preferably above 45 C., and that the insecticide/fungicide mixture is soluble or emulsifiable in this solvent mixture.
In a preferred embodiment, part of the organochemical solvent or solvent mixture is replaced by an aliphatic polar organochemical solvent or solvent mixture. Substances which are preferably used are aliphatic organochemical solvents having hydroxyl and/or ester and/or ether groups, such as, for example, glycol ethers, esters and the like.
The organochemical binders used within the scope of the present invention are the synthetic resins and/or binding drying oils which are known per se and can be diluted with water and/or are soluble or dispersible or emulsifiable in the organochemical solvents employed, in particular binders composed of; or comprising, an acrylate resin, a vinyl resin, for example polyvinyl acetate, polyester resin, polycondensation or polyaddition resin, polyurethane resin, alkyd resin or modified alkyd resin, phenol resin, hydrocarbon resin, such as indene/coumarone resin, silicone resin, drying vegetable and/or drying oils and/or physically drying binders based on a natural and/or synthetic resin.
The synthetic resin used as the binder can be employed in the form of an emulsion, dispersion or solution. Up to 10% by weight of bitumen or bituminous substances can also be used as binder. In addition, colorants, pigments, water repellants, odour-masking substances and inhibitors or anticorrosives known per se and the like can also be employed.
The composition or the concentrate preferably comprises, in accordance with the invention, at least one alkyd resin or modified alkyd resin and/or a drying vegetable oil as the organochemical binder. Preferably used according to the invention are alkyd resins with an oil content of over 45% by weight, preferably 50 to 68% by weight.
All or some of the abovementioned binder can be replaced by a fixative (mixture) or a plasticizer (mixture). These additives are intended to prevent volatilization of the active compounds and crystallization or precipitation. They preferably replace 0.01 to 30% of the binder (based on 100% of binder employed).
The plasticizers are from the chemical classes of the phthalic esters, such as dibutyl phthalate, dioctyl phthalate or benzylbutyl phthalate, the phosphoric esters, such as tributyl phosphate, the adipic esters, such as di-(2-ethylhexyl) adipate, the stearates, such as butyl stearate or amyl stearate, the oleates, such as butyl oleate, the glycerol ethers or relatively high-molecular-weight glycol ethers, glycerol esters and p-toluenesulphonic esters.
Fixatives are chemically based on polyvinyl alkyl ethers, such as, for example, polyvinyl methyl ether, or ketones, such as benzophenone or ethylenebenzophenone.
Particularly suitable as a solvent or diluent is also water, if appropriate as a mixture with one or more of the abovementioned organochemical solvents or diluents, emulsifiers and dispersants.
Particularly effective protection of wood is achieved by large-scale industrial impregnation processes, for example vacuum, double-vacuum or pressure processes.
If appropriate, the ready-to-use compositions can additionally comprise other insecticides and, if appropriate, additionally one or more fungicides.
Suitable additional components which may be admixed are, preferably, the insecticides and fungicides mentioned in WO 94/29 268. The compounds mentioned in that document are expressly incorporated into the present application by reference.
Very particularly preferred components which may be admixed are insecticides, such as chlorpyrifos, phoxim, silafluofin, alphamethrin, cyfluthrin, cypermethrin, deltamethrin, permethrin, imidacloprid, NI-25, flufenoxuron, hexaflumuron and triflumuron, and fungicides, such as epoxyconazole, hexaconazole, azaconazole, propiconazole, tebuconazole, cyproconazole, metconazole, imazalil, diclofluanid, tolylfluanid, 3-iodo-2propinyl-butyl carbamate, N-octyl-isothiazolin-3-one and 4,5-dichloro-N-octylisothiazolin-3-one.